$114 Cheap Flights from Chicago (MDW) to Oakland (OAK)

View $114 flight on Tue, Dec 9, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Oakland Intl. Airport (OAK)

Cheap Flights from Chicago to Oakland (MDW-OAK)

Prices were available within the past 7 days and start at $114 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jan 14 - Sat, Jan 17
MDW
Chicago
OAK
Oakland
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Sat, Jan 17, priced at $239 found 6 days ago
Southwest Airlines
Wed, Dec 17 - Sat, Jan 10
MDW
Chicago
OAK
Oakland
$241 Roundtrip, found 3 days ago
$241
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 17 from Chicago to Oakland, returning Sat, Jan 10, priced at $241 found 3 days ago
Southwest Airlines
Wed, Jan 14 - Sat, Jan 17
MDW
Chicago
OAK
Oakland
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Sat, Jan 17, priced at $249 found 6 days ago
Southwest Airlines
Wed, Jan 14 - Wed, Jan 21
MDW
Chicago
OAK
Oakland
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Wed, Jan 21, priced at $253 found 3 days ago
Southwest Airlines
Wed, Jan 14 - Sat, Jan 17
MDW
Chicago
OAK
Oakland
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Sat, Jan 17, priced at $257 found 6 days ago
Southwest Airlines
Wed, Dec 17 - Sat, Jan 10
MDW
Chicago
OAK
Oakland
$258 Roundtrip, found 3 days ago
$258
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 17 from Chicago to Oakland, returning Sat, Jan 10, priced at $258 found 3 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
MDW
Chicago
OAK
Oakland
$260 Roundtrip, found 1 day ago
$260
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Oakland, returning Sat, Dec 6, priced at $260 found 1 day ago
Southwest Airlines
Wed, Jan 14 - Wed, Jan 21
MDW
Chicago
OAK
Oakland
$261 Roundtrip, found 3 days ago
$261
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Wed, Jan 21, priced at $261 found 3 days ago
Southwest Airlines
Thu, Jan 8 - Sat, Jan 10
MDW
Chicago
OAK
Oakland
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Jan 8 from Chicago to Oakland, returning Sat, Jan 10, priced at $263 found 5 days ago
Delta
Tue, Jan 13 - Sun, Jan 18
MDW
Chicago
OAK
Oakland
$305 Roundtrip, found 3 days ago
$305
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 13 from Chicago to Oakland, returning Sun, Jan 18, priced at $305 found 3 days ago

Find the cheapest month to fly from Chicago (MDW) to Oakland (OAK)

August is typically the cheapest month to fly

From $189 - $672 per traveler.

Alternative airports near Oakland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Francisco Intl. SFO. Average driving time to city center is 32 minutes. Flights from $534
SFO
San Francisco Intl.
Average driving time to city center32 min
Flights from $534
Select flight to Norman Y. Mineta San Jose Intl. SJC. Average driving time to city center is 44 minutes. Flights from $547
SJC
Norman Y. Mineta San Jose Intl.
Average driving time to city center44 min
Flights from $547

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) cost?
Snag a cheap one-way flight from $114 or cheap return flight from $239 from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
The cheapest month to fly from MDW to OAK is January, when there's less demand. Off-peak months are often when airlines offer better prices between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
If you're departing from Midway Intl. Airport (MDW), you can take a nonstop flight to Oakland Intl. Airport (OAK) with Southwest Airlines.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to OAK flight.
How many flights per day from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
On average, just 1 direct flight departs daily from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK). Want additional options? Use Expedia's filters to discover flights with layovers and add an extra destination to your journey.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
Flights between MDW and OAK tend to be busiest at 9 AM. For a more relaxed trip and potentially cheaper fares, look for a time when demand is lower.
What day of the week has the most flights from MDW to OAK?
Friday offers the most flights from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
Take the earliest flight at around 9:40AM UTC-6, departing from Midway Intl. Airport (MDW). You'll be in the air for about 4h 55m, landing at Oakland Intl. Airport (OAK) at approximately 12:35PM UTC-8.
How long does it take to fly from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
Flights from MDW to OAK have an average travel time of 4 hours and 53 minutes. The total distance between the two airports is 1,850 mi.
What airline has the least delays from MDW to OAK?
Consider traveling with Southwest Airlines if you'd like to go straight from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) without any holdups. This carrier has the best track record for punctuality, with an on-time score of 89%. Want to get notified of any changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) route, travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Oakland from Midway Intl. Airport (MDW)?
Hop on a direct flight from Midway Intl. Airport (MDW) to Oakland and you'll land at any one of these hubs:

  • San Francisco Intl. Airport (SFO)
  • Norman Y. Mineta San Jose Intl. Airport (SJC)
  • Oakland Intl. Airport (OAK)

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK) last-minute?
Booking your ticket from MDW to OAK just before your getaway is generally more expensive. But if there's some wiggle room with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to OAK flight and hotel package?
You'll generally save money by securing a MDW to OAK flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your preferred accommodations and flights, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK)?
In most instances, you're able to reschedule or cancel your MDW to OAK flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you want further details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Oakland Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$239
Distance
1840 mi
Average flight time
2 hours 37 mins

Book with confidence

Chicago to Oakland Flights

The cheapest times to fly from Chicago to Oakland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Oakland are during the month of January. You can find some of the cheapest flights from Chicago to Oakland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Oakland

Sunday is one of the best days to book for cheap flights from Chicago to Oakland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Oakland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Oakland in 2025. You can also book with separate airlines for your outbound and return journeys, from $114 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Oakland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Oakland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Oakland Flights

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*Available to One Key members.